Practical Organic Chemistry III: Acetanilide
31 Questions
0 Views

Choose a study mode

Play Quiz
Study Flashcards
Spaced Repetition
Chat to Lesson

Podcast

Play an AI-generated podcast conversation about this lesson

Questions and Answers

Acetanilide is currently used as a sedative or antipyretic.

False (B)

Acetanilide is used as a base for manufacturing other drugs, such as ______.

paracetamol (PCT)

What is the condition that can be caused by an overdose of acetanilide?

Methemoglobinemia

Which of the following mechanisms explains how acetanilide leads to methemoglobinemia?

<p>Inhibition of the enzyme that converts methemoglobin back to hemoglobin (B)</p> Signup and view all the answers

Match the following terms with their descriptions:

<p>Acetanilide = A drug that is no longer used as a sedative or antipyretic due to the risk of methemoglobinemia Methemoglobinemia = A condition where the iron in hemoglobin is oxidized, reducing its ability to carry oxygen Paracetamol (PCT) = A drug that is manufactured using acetanilide as a base</p> Signup and view all the answers

What is the primary reason for dyspnea (difficulty breathing) in methemoglobinemia?

<p>Deficiency of oxygen in the blood (B)</p> Signup and view all the answers

What is the purpose of boiling the liquid for 10 minutes?

<p>To allow condensation to form (B)</p> Signup and view all the answers

Methemoglobinemia is caused by a substance that prevents the binding of oxygen to hemoglobin.

<p>True (A)</p> Signup and view all the answers

The liquid should be heated to evaporate it.

<p>False (B)</p> Signup and view all the answers

What is the chemical formula for the iron ion in hemoglobin that is unable to bind oxygen in methemoglobinemia?

<p>Fe+3</p> Signup and view all the answers

What is the purpose of adding the hot liquid to 50 ml cold water?

<p>To form crystals</p> Signup and view all the answers

What is used as a solvent in the preparation process?

<p>Glacial acetic acid (C)</p> Signup and view all the answers

If the crystals are white and shiny, they are considered ______.

<p>pure</p> Signup and view all the answers

Match the following terms with their corresponding definitions:

<p>Methemoglobinemia = A condition where hemoglobin is unable to bind oxygen Acetanilide = A substance that can oxidize ferrous iron in hemoglobin Dyspnea = Difficulty breathing Fe+3 = Ferric iron, the oxidized form of iron in hemoglobin unable to bind oxygen</p> Signup and view all the answers

The chemical reaction involving acetanilide and ferrous iron (Fe+2) results in the formation of ______, which is unable to carry oxygen.

<p>ferric iron (Fe+3)</p> Signup and view all the answers

Match the apparatus with their corresponding usage during the preparation process:

<p>Beaker = Holding liquid mixtures Ice bath = Cooling reaction Conical flask = Reacting the chemicals Funnel = Pouring liquids into containers</p> Signup and view all the answers

What is one of the uses of para-nitro acetanilide?

<p>Manufacturing pesticides (B)</p> Signup and view all the answers

The mixture consists of ___ ml of H2SO4 as part of preparing nitrite.

<p>1.5</p> Signup and view all the answers

Concentrated sulfuric acid is used in the first step of the preparation process.

<p>True (A)</p> Signup and view all the answers

What is the molecular weight of HNO3?

<p>63 g/mole (D)</p> Signup and view all the answers

How many milliliters of HNO3 are used in the preparation process?

<p>2</p> Signup and view all the answers

Acetanilide is the limiting agent in the reaction described.

<p>True (A)</p> Signup and view all the answers

What is the theoretical mole of acetanilide used?

<p>0.0296 mole</p> Signup and view all the answers

Para-nitro acetanilide is primarily used for the preparation of non-drug compounds.

<p>False (B)</p> Signup and view all the answers

Name one compound that can be prepared from para-nitro acetanilide.

<p>Paracetamol</p> Signup and view all the answers

The molecular weight of P-acetanilide is ______ g/mole.

<p>180</p> Signup and view all the answers

Para-nitro acetanilide is used as a base for the preparation of __________.

<p>paracetin</p> Signup and view all the answers

Match the following substances with their corresponding weights in grams:

<p>Acetanilide = 4 g HNO3 = 2.4 g P-acetanilide = ---- Total mole acetanilide = 0.0296 mole</p> Signup and view all the answers

Match the following uses of para-nitro acetanilide with their descriptions:

<p>1 = Manufacturing pesticides 2 = Base for drug preparation 3 = Uses in rubber production 4 = Preparation of paracetamol</p> Signup and view all the answers

Signup and view all the answers

Signup and view all the answers

Flashcards

Acetanilide

A chemical compound used as a base for making drugs like paracetamol.

Methemoglobinemia

A condition where hemoglobin cannot effectively release oxygen to body tissues.

Drug Manufacturing

The process of creating pharmaceuticals from various compounds.

Overdose Effects

Adverse reactions resulting from consuming too much of a drug.

Signup and view all the flashcards

Sedative

A drug that calms or induces sleep in a patient.

Signup and view all the flashcards

Symptoms of Methemoglobinemia

Common symptoms include dyspnea, fatigue, and cyanosis due to lack of oxygen.

Signup and view all the flashcards

Oxidized Iron

Ferric iron (Fe+3) which is formed when hemoglobin is oxidized, reducing its oxygen-carrying ability.

Signup and view all the flashcards

Reduction of Hemoglobin

The process where ferrous iron (Fe+2) in hemoglobin is converted to ferric iron (Fe+3), impairing oxygen transport.

Signup and view all the flashcards

Boiling

Heating a liquid to its boiling point to create vapor.

Signup and view all the flashcards

Condensation

The process where vapor cools and turns back into liquid.

Signup and view all the flashcards

Crystallization

The process of forming solid crystals from a liquid solution.

Signup and view all the flashcards

Filtration

A method to separate solids from liquids by passing through a filter.

Signup and view all the flashcards

Purity Test

Identifying the purity of crystals based on their color or appearance.

Signup and view all the flashcards

Glacial Acetic Acid

A concentrated form of acetic acid used as a solvent.

Signup and view all the flashcards

Concentrated H2SO4

Sulfuric acid in its pure, undiluted form, often used in reactions.

Signup and view all the flashcards

Nitric Acid (HNO3)

A colorless acid used in nitration processes to produce nitrites.

Signup and view all the flashcards

Ice Bath

A cooling setup used to lower the temperature during reactions.

Signup and view all the flashcards

Filter Paper

Semipermeable paper used to separate solids from liquids in experiments.

Signup and view all the flashcards

Uses of para-nitro acetanilide

It is used in the manufacturing of pesticides and rubber, and as a base for drugs.

Signup and view all the flashcards

Paracetamol

A medication derived from para-nitro acetanilide, commonly used as a pain reliever.

Signup and view all the flashcards

Paracetin

Another compound that can be prepared from para-nitro acetanilide, used in pain relief.

Signup and view all the flashcards

Ortho vs. Para Position

The para position of nitro acetanilide is favored for stability over the ortho position.

Signup and view all the flashcards

Nitro acetanilide Formation

It forms more at the para position due to steric and electronic factors.

Signup and view all the flashcards

Theoretical vs Practical Moles

Theoretical moles are calculated; practical moles are experimentally measured.

Signup and view all the flashcards

Limiting Agent

The reactant that is completely consumed in a chemical reaction, limiting the amount of product formed.

Signup and view all the flashcards

Molecular Weight (MW)

The weight of a molecule, measured in grams per mole (g/mole).

Signup and view all the flashcards

Total Moles Calculation

Total moles represent the sum of reactants based on their weights and molecular weights.

Signup and view all the flashcards

Study Notes

Practical Organic Chemistry III

  • Course Instructor: Abdulrahman Al-Ahedal
  • Scientific Committee: Pharmacists
  • Committee Chair: Abdullah Al-Jubli
  • Committee Member: Fatima Al-Dubayi

Preparation of Acetanilide

  • Chemical Structure: Benzene ring, amino group, acetyl group
  • Type of Reaction: Nucleophilic substitution (acetylation)
  • Molecular Weight (M.Wt): 135 g/mol
  • Physical Properties: White crystals, insoluble in cold water, soluble in hot water, melting point (M.P.) of 113°C (impurities lower the M.P.). Soluble in acetone and chloroform.
  • Clinical Uses: Antipyretic, analgesic, moderate headache sedative.
  • Caution: Overdose causes methemoglobinemia.

Mechanism of Methemoglobinemia

  • Natural hemoglobin: globin + ferrous iron (Fe2+)
  • Acetanilide overdose oxidizes iron to ferric iron (Fe3+), forming methemoglobin. This form of hemoglobin cannot carry oxygen.

Symptoms of Methemoglobinemia

  • Dyspnea (shortness of breath)
  • Skin rash
  • Jaundice

Procedure for Preparing Acetanilide (Method 1)

  • Materials Required: Aniline (9 ml), Acetic Anhydride (15 ml), Acetic acid (15 ml) (as catalyst), Beaker, Conical Flask, Reflux Condenser
  • Steps:
    1. Add Acetic Anhydride and Acetic acid to a beaker.
    2. Add Aniline to a conical flask.
    3. Pour the contents of the beaker into the flask.
    4. Attach the condenser.
    5. Heat for 10 minutes.
    6. Pour the hot solution into cold water to form crystals.
    7. Filter the crystals.

Procedure for Preparing Acetanilide (Method 2)

  • Materials Required: Aniline (9 ml), Acetic Anhydride (11 ml), Acetic acid (18 ml) (as catalyst), Beaker, Ice bath, Conical flask, funnel, filter paper
  • Steps:
    1. Place Aniline in a beaker and immerse it in an ice bath
    2. Add Acetic acid slowly with continuous stirring.
    3. Add Acetic anhydride slowly with continuous stirring.
    4. Continue stirring until crystals form.
    5. Allow the solution to sit at room temp for 10–15 minutes.
    6. Return to ice bath to complete crystal formation.
    7. Perform filtration, dry, and weigh the crystals.

Purification Methods

  • Crystallization: Purification method for solids; filtration of hot solutions.
  • Recrystallization: Repeated filtration at different temperatures.
  • Decolorization: Removal of colored impurities by adding activated charcoal and heating.
  • Sublimation: Purification of solids that pass directly from a solid state to a gas state.
  • Extraction and Filtration: Methods to remove undesirable substances.

Calculation of Yield

  • Formula: [(Experimental Yield / Theoretical Yield) x 100]
  • Density of Aniline: 1.022 g/mL
  • Density of Acetic anhydride: 1.08 g/mL

Nitration of Acetanilide

  • Principle of Reaction: Acetanilide reacted with nitrating mixture (a mixture of HNO3 and H2SO4) under refrigerated conditions to yield p-nitroacetanilide.
  • Procedure:
  1. In a beaker add acetanilide.
  2. Add glacial acetic acid.
  3. Slowly add prepared nitrating mixture (HNO3 and H2SO4) with continuous stirring (exothermic reaction).
  4. Transfer the beaker containing the mixture into an ice bath.
  5. Prepare the nitrating mixture in an ice bath.
  6. Gradually add the nitrating mixture to the acetanilide mixture while stirring.
  7. Let the remaining reaction mixture sit in a cold-water bath for about 30 to 60 minutes with continuous stirring.
  8. Add 100 mL of cold water to precipitate the product.
  9. Perform hot filtration, dry product,and obtain the yield.

Preparation of Salicylamide

  • Chemical Structure: a-hydroxybenzamide
  • Physical Properties: White crystalline powder, Insoluble in cold water, soluble in hot water and basic solutions (e.g., NaOH).
  • Principle of Reaction: Methyl salicylate (ester) is converted to salicylamide (amide) through a reaction with ammonia.
  • Procedure:
  1. Add methyl salicylate and ammonia to a flask.
  2. Shake well until a rosy colour is obtained.
  3. Leave to form a deep violet solution.
  4. Remove excess ammonia through evaporation.
  5. Collect and weigh the product
  • Different from aspirin because of the presence of an amide group
  • Aspirin- contains an ester group.

Distillation

  • Methods: Simple, Fractional, Vacuum, and Steam distillation
  • Types of Distillation and their use cases:
  • Simple Distillation: used to separate liquids with significantly different boiling points.
  • Fractional Distillation: used to separate liquids with similar boiling points.
  • Vacuum Distillation: used for liquids with high boiling points to reduce the temperature needed for vaporization.
  • Steam Distillation: used to separate heat-sensitive substances that are immiscible with water.

Studying That Suits You

Use AI to generate personalized quizzes and flashcards to suit your learning preferences.

Quiz Team

Related Documents

Practical Organic Chemistry III PDF

Description

This quiz focuses on the preparation and properties of acetanilide, a compound used in clinical applications. It covers its chemical structure, type of reaction, and the mechanism of methemoglobinemia caused by overdose. Test your knowledge on the importance and effects of this compound in organic chemistry.

More Like This

Use Quizgecko on...
Browser
Open
Browser
Browser